Hydrochloric Acid → HCID 15645976, compound

HRID 1196877Notes

Reaction equation

HRID 1196877 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH:13]2[CH:25]=O)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:27]1[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]1.Cl.[Na].C([BH3-])#N>CO>[NH3:12].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH:13]2[CH2:25][N:27]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 982104-HydroxypyrrolidineHCID 156459541-[(3,4-Dichlorophenyl)acetyl]-4-(phenylmethyl)-2-piperazine carboxaldehydeHCID 131717404HCID 131717404, compound

Product 2

HCID 222AmmoniaHCID 15645976HCID 15645976, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of the product of stage (ii) (3.67 g) in methanol (60 ml) was added to a stirred suspension of 3-pyrrolidinol (982 mg) and 3 Å molecular sieves (3.68 g) in methanol (35 ml), followed by adjustment of the pH to 6 using methanolic hydrogen chloride solution. Sodium-cyanoborohydride (1.30 g) was added portionwise and the resulting suspension was stirred under nitrogen for 19 h. The suspension was filtered and the filtrate evaporated to dryness. The residue was partitioned between aqueous 2N sodium carbonate solution (150 ml) and dichloromethane (100 ml) and the aqueous layer was further extracted with dichloromethane (2×50 ml)). The combined organic extracts were dried and evaporated to give an oil, which was purified by dry flash column chromatography on silica gel eluting with a mixture of dichloromethane:methanol:0.880 NH3 (200:8:1) to give the title compound as a foam (2.38 g).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated to dryness
  3. customThe residue was partitioned between aqueous 2N sodium carbonate solution (150 ml) and dichloromethane (100 ml)
  4. extractionthe aqueous layer was further extracted with dichloromethane (2×50 ml))
  5. customThe combined organic extracts were dried
  6. customevaporated
  7. customto give an oil, which
  8. customwas purified
  9. customby dry flash column chromatography on silica gel eluting
  10. additionwith a mixture of dichloromethane

Sources & evidence

ORD record
ord-bb92b9268be5490e90dfd9b3c2a9cb20
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

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